ES2779007T3 - Radiation-curable coating agent, process for producing scratch-resistant coatings, use of coating agent and substrate coated with a coating agent - Google Patents
Radiation-curable coating agent, process for producing scratch-resistant coatings, use of coating agent and substrate coated with a coating agent Download PDFInfo
- Publication number
- ES2779007T3 ES2779007T3 ES17700809T ES17700809T ES2779007T3 ES 2779007 T3 ES2779007 T3 ES 2779007T3 ES 17700809 T ES17700809 T ES 17700809T ES 17700809 T ES17700809 T ES 17700809T ES 2779007 T3 ES2779007 T3 ES 2779007T3
- Authority
- ES
- Spain
- Prior art keywords
- coating agent
- weight
- agent according
- coating
- acrylate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000011248 coating agent Substances 0.000 title claims abstract description 120
- 239000006120 scratch resistant coating Substances 0.000 title claims abstract description 10
- 239000000758 substrate Substances 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 6
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical group OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000007787 solid Substances 0.000 claims abstract description 21
- 239000006096 absorbing agent Substances 0.000 claims abstract description 20
- -1 diol diacrylate ester Chemical class 0.000 claims abstract description 18
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 18
- 239000004417 polycarbonate Substances 0.000 claims abstract description 18
- 239000013638 trimer Substances 0.000 claims abstract description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 14
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000000178 monomer Substances 0.000 claims abstract description 13
- 229920000728 polyester Polymers 0.000 claims abstract description 12
- 239000000654 additive Substances 0.000 claims abstract description 8
- 150000001412 amines Chemical class 0.000 claims abstract description 8
- 230000000996 additive effect Effects 0.000 claims abstract description 7
- FHOIVKVRWCOMTB-UHFFFAOYSA-N 1-(2h-triazol-4-yl)prop-2-en-1-one Chemical compound C=CC(=O)C=1C=NNN=1 FHOIVKVRWCOMTB-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000002148 esters Chemical class 0.000 claims abstract description 4
- 238000000576 coating method Methods 0.000 claims description 27
- 230000005855 radiation Effects 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000002966 varnish Substances 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 4
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000005690 diesters Chemical class 0.000 claims description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims 2
- 150000003852 triazoles Chemical class 0.000 claims 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 abstract description 11
- 239000011521 glass Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000001723 curing Methods 0.000 description 5
- 239000004922 lacquer Substances 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 230000008961 swelling Effects 0.000 description 5
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 4
- LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 230000003711 photoprotective effect Effects 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical group C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
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- 150000002513 isocyanates Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 230000004224 protection Effects 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
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- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- KCZQSKKNAGZQSZ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)-1,3,5-triazin-2,4,6-trione Chemical compound O=C=NCCCCCCN1C(=O)N(CCCCCCN=C=O)C(=O)N(CCCCCCN=C=O)C1=O KCZQSKKNAGZQSZ-UHFFFAOYSA-N 0.000 description 1
- OQLGONMRDHLOSE-UHFFFAOYSA-N 1-(4-phenyl-2H-benzotriazol-5-yl)prop-2-en-1-one Chemical compound C(=O)(C=C)C1=C(C2=C(NN=N2)C=C1)C1=CC=CC=C1 OQLGONMRDHLOSE-UHFFFAOYSA-N 0.000 description 1
- WAGRIKSHWXFXHV-UHFFFAOYSA-N 1-hydroxybutyl prop-2-enoate Chemical compound CCCC(O)OC(=O)C=C WAGRIKSHWXFXHV-UHFFFAOYSA-N 0.000 description 1
- ZAXXZBQODQDCOW-UHFFFAOYSA-N 1-methoxypropyl acetate Chemical compound CCC(OC)OC(C)=O ZAXXZBQODQDCOW-UHFFFAOYSA-N 0.000 description 1
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 description 1
- SITYOOWCYAYOKL-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(3-dodecoxy-2-hydroxypropoxy)phenol Chemical compound OC1=CC(OCC(O)COCCCCCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 SITYOOWCYAYOKL-UHFFFAOYSA-N 0.000 description 1
- YMUQRDRWZCHZGC-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO.CCC(CO)(CO)CO YMUQRDRWZCHZGC-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- 241000282485 Vulpes vulpes Species 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000010504 bond cleavage reaction Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000011527 polyurethane coating Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000003678 scratch resistant effect Effects 0.000 description 1
- 239000007779 soft material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09D175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/06—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation
- B05D3/061—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation using U.V.
- B05D3/065—After-treatment
- B05D3/067—Curing or cross-linking the coating
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
- B05D7/02—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to macromolecular substances, e.g. rubber
- B05D7/04—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to macromolecular substances, e.g. rubber to surfaces of films or sheets
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
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- C08F220/343—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate in the form of urethane links
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/006—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
- C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/68—Unsaturated polyesters
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/694—Polymers of conjugated dienes containing carboxylic ester groups
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/80—Masked polyisocyanates
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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Abstract
Agente de recubrimiento endurecible por radiacion, particularmente para producir un revestimiento resistente a los aranazos sobre superficies de policarbonato, conteniendo al menos un acrilato de uretano elaborado a partir de un trimero de isocianurato del diiosocinato de 1,6-hexametileno y mono-acrilato de butanodiol, donde el trimero de isocianurato tiene un contenido en NCO del 19,6 al 24,0% en peso y un peso equivalente de 175 a 214, el acrilato de uretano tiene una razon de pesos del trimero de isocianurato al mono-acrilato de butanodiol de 1,0:0,65 a 1,0:0,9, caracterizado porque el agente de recubrimiento contiene i) del 45,0 al 59,0% en peso del al menos un acrilato de uretano, ii) del 25,0 al 37,0% en peso de al menos un monomero de acrilato de poliester tetrafuncional, iii) del 8,0 al 12,0% en peso de al menos un ester de diacrilato de diol y/o de al menos un ester de monoacrilato iv) del 2,3 al 3,5% en peso de al menos un fotoiniciador v) del 2,1 al 3,1% en peso de al menos un absorbente de UV reactivo de tipo acriltriazol vi) del 1,5 al 2,0% en peso de al menos un absorbente de UV no reactivo vii) del 0,7 al 1,0% en peso de al menos una amina estericamente impedida, viii) del 0,4 al 0,9% en peso de al menos un aditivo de flujo donde los rangos porcentuales en peso se refieren a la suma de los contenidos en solidos de los componentes i) a viii) mencionados y su suma asciende al 100% en peso.Radiation-curable coating agent, particularly for producing a scratch-resistant coating on polycarbonate surfaces, containing at least one urethane acrylate made from a 1,6-hexamethylene diiosocinate isocyanurate trimer and butanediol mono-acrylate , where isocyanurate trimer has an NCO content of 19.6 to 24.0% by weight and an equivalent weight of 175 to 214, urethane acrylate has a weight ratio of isocyanurate trimer to butanediol mono-acrylate from 1.0: 0.65 to 1.0: 0.9, characterized in that the coating agent contains i) 45.0 to 59.0% by weight of the at least one urethane acrylate, ii) 25, 0 to 37.0% by weight of at least one tetrafunctional polyester acrylate monomer, iii) 8.0 to 12.0% by weight of at least one diol diacrylate ester and / or of at least one ester of monoacrylate iv) 2.3 to 3.5% by weight of at least one photoinitiator v) 2.1 to 3.1% by weight of at least a reactive UV absorber of the acryltriazole type vi) from 1.5 to 2.0% by weight of at least one non-reactive UV absorber vii) from 0.7 to 1.0% by weight of at least one sterically hindered amine , viii) from 0.4 to 0.9% by weight of at least one flow additive where the percentage ranges by weight refer to the sum of the solids contents of components i) to viii) mentioned and their sum amounts 100% by weight.
Description
DESCRIPCIÓNDESCRIPTION
Agente de recubrimiento endurecible por radiación, procedimiento para producir revestimientos resistentes a los arañazos, empleo del agente de recubrimiento y sustrato recubierto con un agente de recubrimientoRadiation-curable coating agent, process for producing scratch-resistant coatings, use of coating agent and substrate coated with a coating agent
La presente invención se relaciona con un agente de recubrimiento endurecible por radiación, particularmente para producir un revestimiento resistente a los arañazos sobre superficies de policarbonato, conteniendo al menos un acrilato de uretano de un trímero de isocianurato del diisocianato de 1,6-hexametileno y mono-acrilato de butanodiol. La invención se relaciona también con un procedimiento para la producción de revestimientos resistentes a los arañazos sobre superficies de policarbonato, el empleo del agente de recubrimiento y un sustrato recubierto correspondientemente.The present invention relates to a radiation curable coating agent, particularly for producing a scratch resistant coating on polycarbonate surfaces, containing at least one urethane acrylate of an isocyanurate trimer of 1,6-hexamethylene diisocyanate and mono -butanediol acrylate. The invention also relates to a process for the production of scratch resistant coatings on polycarbonate surfaces, the use of the coating agent and a correspondingly coated substrate.
Se sabe que los vidrios o paneles de los faros de los vehículos han de tener un rendimiento óptico óptimo, una alta transparencia, una fácil deformabilidad para poder darles la forma deseada, buena robustez (resistencia) y un peso adecuado. Todas estas propiedades no pueden obtenerse con los vidrios o paneles tradicionales hechos de vidrio real. La tendencia actual es reemplazar las láminas de vidrio por láminas de materiales plásticos que son más livianos y más fáciles de deformar. Desde este punto de vista, un material óptimo es el policarbonato, que además tiene propiedades ópticas que son las mismas o casi las mismas que las del vidrio real.It is known that the glasses or panels of the headlights of the vehicles have to have an optimal optical performance, a high transparency, an easy deformability to be able to give them the desired shape, good robustness (resistance) and an adequate weight. All these properties cannot be obtained with traditional glasses or panels made from real glass. The current trend is to replace glass sheets with sheets of plastic materials that are lighter and easier to deform. From this point of view, an optimal material is polycarbonate, which also has optical properties that are the same or almost the same as those of real glass.
Sin embargo, se sabe que el policarbonato es un material particularmente blando y, por tanto, se raya fácilmente, lo que conduce a un deterioro de las propiedades ópticas del panel (del vidrio). Además, la exposición prolongada a la luz solar o a las influencias ambientales y/o a los agentes químicos pueden conducir al envejecimiento, lo que lo vuelve quebradizo y, sobre todo, sufre un amarilleamiento y, por lo tanto, una pérdida de transparencia del panel (del vidrio).However, it is known that polycarbonate is a particularly soft material and therefore it is easily scratched, which leads to a deterioration of the optical properties of the panel (of the glass). Furthermore, prolonged exposure to sunlight or environmental influences and / or chemical agents can lead to aging, which makes it brittle and, above all, suffers from yellowing and therefore a loss of transparency of the panel ( glass).
Para resolver estos problemas, los paneles o cristales para faros, que estén hechos de policarbonato (u otros materiales plásticos similares), tienen que protegerse, al menos en su superficie externa, que está expuesta al medio ambiente durante el uso, aplicando lacas transparentes especiales.To solve these problems, the panels or glasses for headlights, which are made of polycarbonate (or other similar plastic materials), have to be protected, at least on their external surface, which is exposed to the environment during use, by applying special clear lacquers .
Un agente de recubrimiento endurecible por radiación del tipo mencionado se conoce gracias a la DE 696 15819 T2. Si bien el agente de recubrimiento conocido conlleva una buena protección de los paneles o vidrios de plástico para los faros de los vehículos contra arañazos e influencias meteorológicas, todavía es necesario mejorar aún más este paso. El agente de recubrimiento conocido tiene además la desventaja de que ha de aplicarse con un alto grosor de capa para alcanzar una protección suficiente. Así, el grosor de la película seca de las capas de laca producidas con el agente de recubrimiento conocido es de al menos 20 mm, de hecho, preferentemente de al menos 25 mm. Estos grosores de capa conducen a un alto consumo de material y hoy ya no son apropiados.A radiation-curable coating agent of the type mentioned is known from DE 696 15819 T2. Although the known coating agent provides good protection of the plastic panels or glass for vehicle headlights against scratches and weather influences, this step still needs to be further improved. The known coating agent also has the disadvantage that it has to be applied with a high layer thickness in order to achieve sufficient protection. Thus, the dry film thickness of the lacquer layers produced with the known coating agent is at least 20 mm, in fact, preferably at least 25 mm. These layer thicknesses lead to high material consumption and are no longer suitable today.
Es un objeto de la presente invención especificar un agente de recubrimiento curable por radiación que sea particularmente apropiado para recubrir superficies de policarbonato y que conduzca a capas de laca endurecidas con resistencia mejorada a los arañazos y a la intemperie con reducido grosor de película seca.It is an object of the present invention to specify a radiation curable coating agent which is particularly suitable for coating polycarbonate surfaces and which leads to cured lacquer layers with improved scratch and weather resistance with reduced dry film thickness.
Este objeto se resuelve conforme a la invención con un agente de recubrimiento endurecible por radiación conteniendo al menos un acrilato de uretano elaborado a partir de un trímero de isocianurato del diisocianato de 1,6-hexametileno y mono-acrilato de butanodiol, donde el trímero de isocianurato tiene un contenido en NCO del 19,6 al 24,0% en peso y un peso equivalente de 175 a 214, el acrilato de uretano tiene una razón de pesos del trímero de isocianurato al mono-acrilato de butanodiol de 1,0:0,65 a 1,0:0,9, caracterizado porque el agente de recubrimiento contieneThis object is solved according to the invention with a radiation-curable coating agent containing at least one urethane acrylate made from an isocyanurate trimer of 1,6-hexamethylene diisocyanate and butanediol mono-acrylate, where the trimer of Isocyanurate has an NCO content of 19.6 to 24.0% by weight and an equivalent weight of 175 to 214, urethane acrylate has a weight ratio of isocyanurate trimer to butanediol mono-acrylate of 1.0: 0.65 to 1.0: 0.9, characterized in that the coating agent contains
i) del 45,0 al 59,0% en peso del al menos un acrilato de uretano,i) 45.0 to 59.0% by weight of the at least one urethane acrylate,
ii) del 25,0 al 37,0% en peso de al menos un monómero de acrilato de poliéster tetrafuncional,ii) 25.0 to 37.0% by weight of at least one tetrafunctional polyester acrylate monomer,
iii) del 8,0 al 12,0% en peso de al menos un éster de diacrilato de diol y/o de al menos un éster de monoacrilato,iii) from 8.0 to 12.0% by weight of at least one diol diacrylate ester and / or of at least one monoacrylate ester,
iv) del 2,3 a 3,5% en peso de al menos un fotoiniciador,iv) 2.3 to 3.5% by weight of at least one photoinitiator,
v) del 2,1 al 3,1% en peso de al menos un absorbente de UV reactivo tipo acril-triazol,v) 2.1 to 3.1% by weight of at least one reactive UV absorber type acryl-triazole,
vi) del 1,5 a 2,0% en peso de al menos un absorbente de UV no reactivo,vi) 1.5 to 2.0% by weight of at least one non-reactive UV absorber,
vii) del 0,7 a 1,0% en peso de al menos una amina estéricamente impedida y vii) 0.7 to 1.0% by weight of at least one sterically hindered amine and
viii) del 0,4 al 0,9% en peso de al menos un aditivo de flujo,viii) 0.4 to 0.9% by weight of at least one flow additive,
donde los rangos de porcentajes en peso se refieren a la suma de los contenidos en sólidos de dichos componentes i) a viii) y cuya suma es del 100% en peso.where the ranges of percentages by weight refer to the sum of the solids contents of said components i) to viii) and whose sum is 100% by weight.
De las reivindicaciones dependientes se derivan configuraciones ventajosas del agente de recubrimiento curable por radiación conforme a la invención.Advantageous embodiments of the radiation-curable coating agent according to the invention follow from the dependent claims.
El contenido en sólidos es la fracción no volátil de una sustancia o composición. El contenido en sólidos se determina según la DIN EN ISO 3251:2008, secando 3 g de la sustancia o composición durante 60 minutos a 60 °C. La fracción no volátil que queda después del secado se relaciona con el peso y da el contenido en sólidos de la sustancia o composición.Solid content is the non-volatile fraction of a substance or composition. The solids content is determined according to DIN EN ISO 3251: 2008, drying 3 g of the substance or composition for 60 minutes at 60 ° C. The non-volatile fraction remaining after drying is related to weight and gives the solid content of the substance or composition.
El contenido en grupos isocianato se determina según la DIN EN ISO 11909.The isocyanate group content is determined according to DIN EN ISO 11909.
A menos que se indique aquí lo contrario, todas las indicaciones de normativa se refieren a la normativa actual en la fecha de presentación de la presente invención.Unless otherwise stated herein, all regulatory statements refer to current regulations as of the filing date of the present invention.
El agente de recubrimiento curable por radiación es preferentemente un agente de recubrimiento que se cura con radiación UV. El curado UV designa una reacción química inducida por rayos UV. La radiación UV es el nombre de aquella parte de la radiación electromagnética que cubre el rango de longitudes de onda de 100 a 400 nm.The radiation curable coating agent is preferably a UV radiation-curable coating agent. UV curing designates a chemical reaction induced by UV rays. UV radiation is the name of that part of electromagnetic radiation that covers the wavelength range of 100 to 400 nm.
El agente de recubrimiento conforme a la invención es además preferentemente un barniz transparente.The coating agent according to the invention is also preferably a transparent varnish.
Acrilato de uretanoUrethane acrylate
Los acrilatos de uretano pueden producirse generalmente por adición de acrilatos de hidroxialquilo, diisocianatos y polioles o por adición directa de acrilatos de hidroxialquilo a poliisocianatos. Permiten combinar el alto nivel de rendimiento y la multitud de posibles usos de los recubrimientos de poliuretano con la velocidad de endurecimiento y y la eficiencia de la fotopolimerización. Los acrilatos de uretano se utilizan en recubrimientos de curado por radiación para aplicaciones industriales.Urethane acrylates can generally be produced by the addition of hydroxyalkyl acrylates, diisocyanates, and polyols or by direct addition of hydroxyalkyl acrylates to polyisocyanates. They make it possible to combine the high level of performance and the multitude of possible uses of polyurethane coatings with the speed of curing and the efficiency of photopolymerization. Urethane acrylates are used in radiation cure coatings for industrial applications.
El agente de recubrimiento conforme a la invención contiene al menos un acrilato de uretano elaborado a partir de un trímero de isocianurato del diisocianato de 1,6-hexametileno y mono-acrilato de butanodiol, donde el trímero de isocianurato tiene un contenido en NCO del 19,6 al 24,0% en peso y un peso equivalente de 175 a 214, el acrilato de uretano tiene una razón en peso del trímero de isocianurato al mono-acrilato de butanodiol de 1:0,65 a 1:0,9.The coating agent according to the invention contains at least one urethane acrylate made from an isocyanurate trimer of 1,6-hexamethylene diisocyanate and butanediol mono-acrylate, where the isocyanurate trimer has an NCO content of 19 At 6 to 24.0% by weight and an equivalent weight of 175 to 214, the urethane acrylate has a weight ratio of isocyanurate trimer to butanediol mono-acrylate of 1: 0.65 to 1: 0.9.
En la DE 696 15819 T2 se usa una resina base en la composición de revestimiento, que está hecha a partir de un trímero de isocianurato de diisocianato de 1,6-hexametileno y mono-acrilato de butanodiol. El compuesto de isocianato utilizado tiene un contenido en NCO del 11,0% en peso y un peso equivalente de 382. En el contexto de la presente invención, se descubrió que la resistencia al rayado y la resistencia a la intemperie de las películas de laca endurecidas resultantes pueden mejorarse mediante un poliisocianato con un mayor contenido en NCO y un menor peso equivalente y mediante una composición modificada de monómeros polimerizables y absorbedores de UV.In DE 696 15819 T2 a base resin is used in the coating composition, which is made from an isocyanurate trimer of 1,6-hexamethylene diisocyanate and butanediol mono-acrylate. The isocyanate compound used has an NCO content of 11.0% by weight and an equivalent weight of 382. In the context of the present invention, it was found that the scratch resistance and the weather resistance of the lacquer films Resulting hardenings can be enhanced by a polyisocyanate with a higher NCO content and a lower equivalent weight and by a modified composition of polymerizable monomers and UV absorbers.
Es esencial para la invención que el agente de recubrimiento contenga del 45.0 al 59.0% en peso del acrilato de uretano hecho a partir de un trímero de isocianurato de diisocianato de 1,6-hexametileno y mono-acrilato de butanodiol relativo a la suma del contenido en sólidos de los componentes i) a viii). La composición de revestimiento contiene preferentemente del 45,0 al 55,0% en peso del correspondiente acrilato de uretano. Si el porcentaje en peso del acrilato de uretano estuviera por debajo del límite mencionado anteriormente, esto conllevaría una reactividad empeorada de los componentes durante el curado del agente de recubrimiento. Si el porcentaje en peso del acrilato de uretano fuera superior al 59,0% en peso, relativo a la suma del contenido en sólidos de los componentes i) a viii) mencionados, esto conduciría a una peor adhesión del recubrimiento resultante del agente de recubrimiento al sustrato al que se aplicó el agente de recubrimiento.It is essential to the invention that the coating agent contains 45.0 to 59.0% by weight of the urethane acrylate made from a 1,6-hexamethylene diisocyanate isocyanurate trimer and butanediol mono-acrylate relative to the sum of the content. in solids of components i) to viii). The coating composition preferably contains 45.0 to 55.0% by weight of the corresponding urethane acrylate. If the percentage by weight of the urethane acrylate were below the limit mentioned above, this would lead to a worse reactivity of the components during the curing of the coating agent. If the percentage by weight of the urethane acrylate were greater than 59.0% by weight, relative to the sum of the solids content of the mentioned components i) to viii), this would lead to a worse adhesion of the resulting coating of the coating agent to the substrate to which the coating agent was applied.
Monómero de acrilato de poliéster tetrafuncionalTetrafunctional Polyester Acrylate Monomer
El agente de recubrimiento conforme a la invención contiene del 25,0 al 37,0% en peso de al menos un monómero de acrilato de poliéster tetrafuncional, relativo a la suma de los contenidos en sólidos de los componentes i) a viii). El agente de recubrimiento contiene preferentemente del 27,0 al 37,0% en peso de al menos un monómero de acrilato de poliéster tetrafuncional, relativo a la suma de los contenidos en sólidos de los componentes i) a viii). The coating agent according to the invention contains 25.0 to 37.0% by weight of at least one tetrafunctional polyester acrylate monomer, based on the sum of the solids contents of components i) to viii). The coating agent preferably contains 27.0 to 37.0% by weight of at least one tetrafunctional polyester acrylate monomer, relative to the sum of the solids contents of components i) to viii).
Si el porcentaje en peso del monómero de acrilato de poliéster tetrafuncional estuviera por debajo del límite mencionado anteriormente, esto conllevaría una adhesión empeorada del revestimiento producido a partir del agente de revestimiento al sustrato al que se ha aplicado el agente de revestimiento. Si el porcentaje en peso del monómero de acrilato de poliéster tetrafuncional estuviera por encima de los límites de porcentaje en peso mencionados anteriormente, esto conduciría a una peor resistencia al rayado del revestimiento resultante.If the weight percent of the tetrafunctional polyester acrylate monomer were below the above-mentioned limit, this would lead to impaired adhesion of the coating produced from the coating agent to the substrate to which the coating agent has been applied. If the weight percent of the tetrafunctional polyester acrylate monomer were above the weight percent limits mentioned above, this would lead to poorer scratch resistance of the resulting coating.
Con respecto al componente ii), es esencial para la invención que éste contenga cuatro unidades de ácido acrílico, es decir, sea tetrafuncional en relación a las unidades de ácido acrílico.With regard to component ii), it is essential for the invention that it contains four acrylic acid units, that is, it is tetrafunctional relative to the acrylic acid units.
El monómero de acrilato de poliéster tetrafuncional tiene preferentemente como elemento estructural adicional átomos de oxígeno en forma de enlaces éter. De manera particularmente preferente, el monómero de acrilato de poliéster tetrafuncional tiene exactamente un enlace éter. La presencia particularmente preferente de un enlace de éter garantiza una resistencia mejorada a los productos químicos del revestimiento producido a partir del agente de recubrimiento. El monómero de acrilato de poliéster tetrafuncional es de manera muy particularmente preferente tetracrilato de di(trimetilolpropano).The tetrafunctional polyester acrylate monomer preferably has as an additional structural element oxygen atoms in the form of ether bonds. Particularly preferably, the tetrafunctional polyester acrylate monomer has exactly one ether bond. The particularly preferred presence of an ether bond ensures improved chemical resistance of the coating produced from the coating agent. The tetrafunctional polyester acrylate monomer is very particularly preferably di (trimethylolpropane) tetracrylate.
Éster de diacrilato de diol/éster de mono-acrilatoDiol diacrylate ester / mono-acrylate ester
Conforme a la invención, el agente de recubrimiento curable por radiación contiene como componente iii) del 8,0 al 12,0% en peso de al menos un éster de diacrilato de diol y/o de al menos un éster de mono-acrilato. De manera particularmente preferente, el agente de recubrimiento contiene del 9,0 al 10,0% en peso de al menos un éster de diacrilato de diol y/o de al menos un éster de mono-acrilato, relativo a la suma de los contenidos en sólidos de los componentes i) a viii). Por consiguiente, el agente de recubrimiento contiene en los porcentajes en peso mencionados anteriormente o bien al menos un éster de diacrilato de diol o al menos un éster de mono-acrilato o una mezcla de al menos un éster de diacrilato de diol y al menos un éster de mono-acrilato, donde se prefiere el uso de ésteres de diacrilato de diol.According to the invention, the radiation-curable coating agent contains as component iii) from 8.0 to 12.0% by weight of at least one diol diacrylate ester and / or of at least one mono-acrylate ester. The coating agent particularly preferably contains from 9.0 to 10.0% by weight of at least one diol diacrylate ester and / or of at least one mono-acrylate ester, relative to the sum of the contents. in solids of components i) to viii). Accordingly, the coating agent contains in the abovementioned weight percentages either at least one diol diacrylate ester or at least one mono-acrylate ester or a mixture of at least one diol diacrylate ester and at least one mono-acrylate ester, where the use of diol diacrylate esters is preferred.
Como éster de mono-acrilato se usan preferentemente acrilato formal de trimetilolpropano, mono-acrilato de butanodiol (4-HBA), acrilato de tetrahidrofurfurilo (THFA), acrilato de octil decilo (ODA) o acrilato de isodecilo (IDA). De manera particularmente preferente se usan mono-acrilato de butanodiol (4-HBA), acrilato de tetrahidrofurfurilo (THFA), acrilato de octil decilo (ODA) o acrilato de isodecilo (IDA).As the mono-acrylate ester, preferably trimethylolpropane formal acrylate, butanediol mono-acrylate (4-HBA), tetrahydrofurfuryl acrylate (THFA), octyl decyl acrylate (ODA) or isodecyl acrylate (IDA) are used. Butanediol monoacrylate (4-HBA), tetrahydrofurfuryl acrylate (THFA), octyl decyl acrylate (ODA) or isodecyl acrylate (IDA) are particularly preferably used.
Como éster de diacrilato de diol se utilizan preferentemente aquellos compuestos, que tengan en la cadena de carbono más larga de 2 a 12 átomos de carbono. Un éster de diacrilato de diol particularmente preferente es el diacrilato de 1,6-hexanodiol.The diol diacrylate ester used is preferably those compounds which have from 2 to 12 carbon atoms in the longest carbon chain. A particularly preferred diol diacrylate ester is 1,6-hexanediol diacrylate.
El uso de porcentaje en peso de ésteres de diacrilato de diol y/o ésteres de mono-acrilato en el agente de recubrimiento conforme a la invención controla la hinchazón del sustrato, particularmente del policarbonato, sobre el que se aplica el agente de recubrimiento, de forma que pueda formarse una llamada capa IPL (capa de interpenetración - Interpenetration Layer). De este modo se garantiza la adhesión del revestimiento al sustrato. La formación de esta llamada capa IPL se logra disolviendo la capa más superior del sustrato de policarbonato. Sin embargo, la disolución no debe ser tan fuerte que afecte a la transparencia del sustrato de policarbonato recubierto y, en consecuencia, se vuelva notable por la aparición de una fuerte neblina. Este "hinchamiento" conduce a una adhesión mejorada al aumentar las superficies de contacto entre el sustrato y el agente de recubrimiento. Además, la hinchazón no puede ser demasiado fuerte, ya que esto conllevaría una estabilidad a la intemperie empeorada. Por otro lado, si el "hinchamiento" fuera demasiado bajo, esto conduciría a una peor adhesión al sustrato.The use of percentage by weight of diol diacrylate esters and / or mono-acrylate esters in the coating agent according to the invention controls the swelling of the substrate, particularly of the polycarbonate, on which the coating agent is applied, from A so-called IPL layer (Interpenetration Layer) can be formed. This ensures adhesion of the coating to the substrate. The formation of this so-called IPL layer is achieved by dissolving the uppermost layer of the polycarbonate substrate. However, the dissolution should not be so strong that it affects the transparency of the coated polycarbonate substrate, and consequently, it becomes noticeable by the appearance of a strong haze. This "swelling" leads to improved adhesion by increasing the contact surfaces between the substrate and the coating agent. Furthermore, the swelling cannot be too strong, as this would lead to a worse weather stability. On the other hand, if the "swelling" were too low, this would lead to poorer adhesion to the substrate.
FotoiniciadorPhotoinitiator
El agente de recubrimiento conforme a la invención contiene del 2,3 al 3,5% en peso de al menos un fotoiniciador, relativo a la suma de los contenidos en sólidos de los componentes i) a viii). Los fotoiniciadores sirven para iniciar la reacción de reticulación bajo la influencia de la radiación.The coating agent according to the invention contains 2.3 to 3.5% by weight of at least one photoinitiator, based on the sum of the solids contents of components i) to viii). Photoinitiators serve to initiate the crosslinking reaction under the influence of radiation.
El al menos un fotoiniciador contiene ventajosamente un compuesto que contiene fósforo. Hay productos comerciales correspondientes disponibles comercialmente bajo el nombre de Irgacure. El fotoiniciador contiene de manera particularmente ventajosa una mezcla de al menos un compuesto que contenga fósforo y al menos una ahidroxicetona aromática.The at least one photoinitiator advantageously contains a phosphorus-containing compound. Corresponding commercial products are commercially available under the name Irgacure. The photoinitiator contains particularly advantageously a mixture of at least one phosphorous-containing compound and at least one aromatic hydroxyketone.
El uso preferente de dos fotoiniciadores diferentes tiene un efecto ventajoso sobre el endurecimiento del agente de recubrimiento, ya que permite el endurecimiento tanto en la superficie del agente de recubrimiento como en la cercanía de la superficie del sustrato.The preferred use of two different photoinitiators has an advantageous effect on the curing of the coating agent, as it allows curing both on the surface of the coating agent and in the vicinity of the surface of the substrate.
Agente fotoprotector Photoprotective agent
El agente de recubrimiento conforme a la invención contiene diferentes agentes fotoprotectores, que contienen una combinación de al menos dos absorbentes de UV y al menos una amina impedida estéricamente como captador de radicales. El objeto del agente fotoprotector es evitar que se formen componentes intermedios químicamente reactivos, que puedan provocar la descomposición de la película de revestimiento reticulada. Los radicales libres procedentes de la división de los enlaces químicos dentro de un recubrimiento, causados por la dañina radiación UV del ambiente, han de ser interceptados y desactivados de esta manera. Los radicales generados por la escisión de un enlace químico conducen a una reacción en cadena dentro del recubrimiento, lo que conduce a más escisiones de enlaces. En consecuencia, el uso de un agente fotoprotector es esencial para la invención a fin de garantizar una buena estabilidad a largo plazo del revestimiento elaborado a partir del agente de recubrimiento conforme a la invención.The coating agent according to the invention contains various photoprotective agents, which contain a combination of at least two UV absorbers and at least one sterically hindered amine as a radical scavenger. The object of the photoresist is to prevent the formation of chemically reactive intermediate components, which can cause decomposition of the crosslinked coating film. Free radicals from the splitting of chemical bonds within a coating, caused by harmful UV radiation from the environment, have to be intercepted and deactivated in this way. The radicals generated by the cleavage of a chemical bond lead to a chain reaction within the coating, which leads to further bond cleavages. Consequently, the use of a photoresist is essential to the invention in order to ensure good long-term stability of the coating made from the coating agent according to the invention.
Absorbente de UVUV absorber
El agente de recubrimiento conforme a la invención contiene la combinación de un absorbente de UV reactivo tipo acriltriazol y de un absorbente de UV no reactivo. El término "reactivo" significa aquí, que el absorbente de Uv reacciona, durante el curado por radiación, con los demás componentes curables por radiación y se polimeriza. Por el contrario, el absorbente de UV no reactivo no reacciona con otros componentes del agente de recubrimiento. El agente de recubrimiento conforme a la invención contiene del 2,1 al 3,1% en peso de al menos un absorbente de UV reactivo tipo acriltriazol y 1,5 a 2,0% en peso de al menos un absorbente de UV no reactivo en cada caso, relativo a la suma de los contenidos en sólidos de los componentes i) a viii).The coating agent according to the invention contains the combination of an acryltriazole-type reactive UV absorber and a non-reactive UV absorber. The term "reactive" here means that the UV absorber reacts, during radiation curing, with the other radiation curable components and polymerizes. In contrast, the non-reactive UV absorber does not react with other components of the coating agent. The coating agent according to the invention contains 2.1 to 3.1% by weight of at least one reactive UV absorber such as acryltriazole and 1.5 to 2.0% by weight of at least one non-reactive UV absorber in each case, relative to the sum of the solids contents of components i) to viii).
El absorbente de UV reactivo tipo acriltriazol es ventajosamente un acril fenil benzotriazol. Éste se integra químicamente en el recubrimiento resultante por la funcionalidad acrilato presente en la molécula durante la reacción de reticulación y, por lo tanto, se fija, de tal forma que se evite la migración. Hay productos comerciales disponibles con el nombre comercial Chisorb 593 de Double Bond Chemical.The acryltriazole reactive UV absorber is advantageously an acryl phenyl benzotriazole. This is chemically integrated into the resulting coating by the acrylate functionality present in the molecule during the crosslinking reaction and is therefore fixed in such a way as to prevent migration. Commercial products are available under the trade name Chisorb 593 from Double Bond Chemical.
El absorbente de UV no reactivo es ventajosamente un compuesto a base de una 1,3,5-triazina. Hay productos comerciales disponibles con el nombre comercial Tinuvin400 de BASF SE (anteriormente Ciba).The non-reactive UV absorber is advantageously a 1,3,5-triazine-based compound. Commercial products are available under the trade name Tinuvin400 from BASF SE (formerly Ciba).
El uso conforme a la invención de una combinación de al menos un absorbente de UV reactivo tipo acriltriazol y de al menos un absorbente de UV no reactivo se asegura de que en el revestimiento elaborado a partir del agente de recubrimiento conforme a la invención la radiación del ambiente se convierta en la correspondiente energía de rotación y vibración de estas moléculas, de tal forma que se eviten daños de enlaces químicos dentro de un revestimiento y, por tanto, pueda evitarse la escisión de enlaces.The use according to the invention of a combination of at least one acryltriazole-type reactive UV absorber and of at least one non-reactive UV absorber ensures that in the coating made from the coating agent according to the invention the radiation of the environment is converted into the corresponding energy of rotation and vibration of these molecules, in such a way that damage of chemical bonds within a coating is avoided and, therefore, the cleavage of bonds can be avoided.
Captador de radicales - amina estéricamente impedidaRadical scavenger - sterically hindered amine
El agente de recubrimiento conforme a la invención contiene del 0,7 al 1,0% en peso de al menos una amina estéricamente impedida, relativo a la suma de los contenidos en sólidos de los componentes i) a viii), que actúan como captadores de radicales.The coating agent according to the invention contains 0.7 to 1.0% by weight of at least one sterically hindered amine, relative to the sum of the solids contents of components i) to viii), which act as scavengers. of radicals.
Como agente fotoprotector a base de aminas estéricamente impedidas se emplea ventajosamente un diéster del ácido sebácico. Hay productos comerciales adecuados disponibles con el nombre comercial Tinuvin123 de BASF SA (anteriormente Ciba).As a photoprotective agent based on hindered amines, a diester of sebacic acid is advantageously used. Suitable commercial products are available under the trade name Tinuvin123 from BASF SA (formerly Ciba).
Aditivos de flujoFlow additives
El agente de recubrimiento conforme a la invención contiene del 0,4 al 0,9% en peso de al menos un aditivo de flujo, relativo a la suma de los contenidos en sólidos de los componentes i) a viii).The coating agent according to the invention contains 0.4 to 0.9% by weight of at least one flow additive, based on the sum of the solids contents of components i) to viii).
Como agente de flujo en el agente de recubrimiento conforme a la invención se usa preferiblemente un polímero modificado con polisiloxano con grupos terminales insaturados. Hay productos comerciales adecuados disponibles bajo la línea de productos EFKA de BASF.As flow agent in the coating agent according to the invention, preferably a polysiloxane-modified polymer with unsaturated end groups is used. Suitable commercial products are available under the EFKA product line from BASF.
El aditivo de flujo es responsable de lograr un buen estado de la laca de acabado, así como de un buen aspecto del revestimiento elaborado a partir del agente de recubrimiento conforme a la invención, particularmente en el caso de que el agente de recubrimiento conforme a la invención se utilice como barniz transparente. En general, los barnices transparentes muestran con grosor de capa suficientemente alto, generalmente a > 25 mm, una buena evolución, que generalmente se deteriora a grosores de capa reducidos. Como el agente de recubrimiento conforme a la invención se aplica preferentemente con grosores de capa bajos en el rango de 8 a 25 mm, el uso de un aditivo de flujo apropiado en el rango del 0,4 al 0,9% en peso de al menos un aditivo de flujo, relativo a la suma de los contenidos en sólidos de los componentes i) a viii) es esencial para la invención. Si se superara el rango de porcentaje en peso mencionado anteriormente, se empeoraría la resistencia al rayado del revestimiento elaborado a partir del agente de recubrimiento.The flow additive is responsible for achieving a good condition of the topcoat, as well as for a good appearance of the coating made from the coating agent according to the invention, in particular when the coating agent according to the invention is used as a clear varnish. In general, transparent varnishes show a sufficiently high layer thickness, generally> 25 mm, a good evolution, which generally deteriorates at low layer thicknesses. Since the coating agent according to the invention is preferably applied with low layer thicknesses in the range of 8 to 25 mm, the use of a suitable flow additive in the range of 0.4 to 0.9% by weight of al Minus one flow additive, relative to the sum of the solids contents of components i) to viii) is essential to the invention. If the range of percent by weight mentioned above, the scratch resistance of the coating made from the coating agent would deteriorate.
DisolventesSolvents
El agente de recubrimiento conforme a la invención se ajusta preferentemente empleando disolventes orgánicos a la viscosidad deseada para la aplicación. el agente de recubrimiento contiene Ventajosamente del 27,0 al 70,0% en peso de disolvente orgánico, relativo al peso total del agente de recubrimiento.The coating agent according to the invention is preferably adjusted using organic solvents to the desired viscosity for the application. the coating agent advantageously contains from 27.0 to 70.0% by weight of organic solvent, relative to the total weight of the coating agent.
Como disolventes orgánicos entran en consideración ventajosamente todos los disolventes orgánicos habituales y conocidos por el experto, que, por un lado, permitan una buena solubilidad de los componentes y, por otro lado, sean conocidos por lograr una buena estabilidad al almacenamiento y permitan un buen comportamiento de aplicación del agente de recubrimiento. Para este propósito son particularmente adecuados alcoholes como el ipropanol y el n-butanol, ésteres como el acetato de n-butilo y el acetato de 1-metoxipropilo y/o las cetonas como la metil etil cetona y la metil isobutil cetona. Al elegir el disolvente o la combinación de disolventes, debe tenerse en cuenta que estos se eligen de tal modo que el sustrato de policarbonato no se hinche tanto cuando se aplica el agente de recubrimiento que la transparencia del agente de recubrimiento se vea afectada negativamente, lo que se hace notable con un elevado Haze o dispersión de la luz. La elección del disolvente también puede influir en la adhesión al sustrato del revestimiento resultante a partir del agente de revestimiento. Sin embargo, se debe tener cuidado de asegurar que los disolventes se seleccionen de tal manera que se logre un buen efecto adherente mediante el hinchamiento del sustrato, pero sin causar una matidez del agente de recubrimiento endurecido.As organic solvents there are advantageously all the usual organic solvents known to the expert, which, on the one hand, allow good solubility of the components and, on the other hand, are known to achieve good storage stability and allow good coating agent application behavior. Alcohols such as ipropanol and n-butanol, esters such as n-butyl acetate and 1-methoxypropyl acetate and / or ketones such as methyl ethyl ketone and methyl isobutyl ketone are particularly suitable for this purpose. When choosing the solvent or combination of solvents, it should be noted that the solvents are chosen such that the polycarbonate substrate does not swell so much when the coating agent is applied that the transparency of the coating agent is adversely affected, thereby which becomes noticeable with high haze or light scattering. The choice of solvent can also influence the adhesion to the substrate of the resulting coating from the coating agent. However, care must be taken to ensure that the solvents are selected in such a way that a good tackifying effect is achieved by swelling the substrate, but without causing a dullness of the cured coating agent.
El ajuste porcentual variable en peso del contenido de disolvente, relativo al peso total del agente de recubrimiento, permite variar ventajosamente el contenido en sólidos del agente de recubrimiento de tal manera que el agente de recubrimiento conforme a la invención se pueda aplicar a un sustrato tanto como recubrimiento por flujo como recubrimiento por pulverización. Para usar en el ámbito de recubrimiento de flujo es ventajoso un contenido en sólidos del 27,0 al 50,0% en peso relativo al peso total del agente de recubrimiento. En el ámbito del revestimiento por pulverización es ventajoso un contenido en sólidos del 60,0 al 70,0% en peso relativo al peso total del agente de recubrimiento. Generalmente pueden lograrse para el agente de recubrimiento conforme a la invención también contenidos en sólidos aún mayores que los mencionados anteriormente, relativo al peso total del agente de recubrimiento. En estos casos, sin embargo, se debe tener cuidado de asegurarse de que el reducido contenido en disolvente, relativo al peso total del agente de recubrimiento, no genere ninguna desventaja respecto al estado de la laca de acabado y el flujo.The variable percentage adjustment by weight of the solvent content, relative to the total weight of the coating agent, makes it possible to advantageously vary the solids content of the coating agent in such a way that the coating agent according to the invention can be applied to a substrate both as a flow coating as a spray coating. For use in the field of flow coating, a solids content of 27.0 to 50.0% by weight relative to the total weight of the coating agent is advantageous. In the field of spray coating, a solids content of 60.0 to 70.0% by weight relative to the total weight of the coating agent is advantageous. In general, even higher solids contents than those mentioned above, relative to the total weight of the coating agent, can be achieved for the coating agent according to the invention. In these cases, however, care must be taken to ensure that the low solvent content, relative to the total weight of the coating agent, does not create any disadvantage with respect to the condition of the topcoat and flow.
La invención se relaciona también con un procedimiento para la producción de revestimientos resistentes a los arañazos sobre superficies de policarbonato mediante i) aplicación de un agente de recubrimiento conforme a la invención sobre una superficie de policarbonato y ii) endurecimiento del agente de recubrimiento con radiación UV. Ventajosamente se aplica el revestimiento resistente a los arañazos con grosores de película seca de 8 a 25 mm, de manera particularmente preferente con grosores de película seca de 10 a 20 mm. la determinación del grosor de película seca de un revestimiento de barniz transparente se lleva a cabo con un interferómetro de luz blanca. La determinación del grosor de película seca de un revestimiento, que no sea ningún recubrimiento de barniz transparente, se realiza por medio de preparación de la sección transversal y posterior examen microscópico de estas secciones transversales.The invention also relates to a process for the production of scratch-resistant coatings on polycarbonate surfaces by i) applying a coating agent according to the invention to a polycarbonate surface and ii) curing the coating agent with UV radiation . The scratch-resistant coating is advantageously applied with dry film thicknesses of 8 to 25 mm, particularly preferably with dry film thicknesses of 10 to 20 mm. the determination of the dry film thickness of a clear varnish coating is carried out with a white light interferometer. Determination of the dry film thickness of a coating, other than a clear varnish coating, is accomplished by preparing the cross section and subsequent microscopic examination of these cross sections.
La invención se refiere además al uso de un agente de recubrimiento conforme a la invención para producir un revestimiento para proteger las superficies de los faros del vehículo contra arañazos e influencias meteorológicas. Finalmente, la invención también se refiere a un sustrato que está recubierto con un agente de recubrimiento endurecido conforme a la invención. El sustrato es preferiblemente un sustrato hecho de policarbonato.The invention further relates to the use of a coating agent according to the invention to produce a coating for protecting the surfaces of vehicle headlights against scratches and weather influences. Finally, the invention also relates to a substrate which is coated with a cured coating agent according to the invention. The substrate is preferably a substrate made of polycarbonate.
A continuación se explica la invención con más detalle en base a ejemplos de ejecución y ejemplos comparativos.The invention is explained in more detail below on the basis of exemplary embodiments and comparative examples.
Ejemplo de producción 1: Producción de acrilato de uretano 1 según la DE 696 15819 T2 (comparativo) La resina base se prepara mezclando los siguientes componentes en las proporciones establecidas (expresadas en gramos): Production example 1: Production of urethane acrylate 1 according to DE 696 15819 T2 (comparative) The base resin is prepared by mixing the following components in the established proportions (expressed in grams):
Ejemplo de producción 2: Producción del acrilato de uretano 2 (conforme a la invención)Production example 2: Production of urethane acrylate 2 (according to the invention)
Se rellenan 170,70 g del trímero de isocianato (Desmodur N3300, compañía Bayer) en un matraz de tres cuellos de 1000 ml. El aparato está equipado con un agitador de cuchillas KPG, un embudo de goteo y una pieza de alimentación de gas para introducir aire pobre.170.70 g of the isocyanate trimer (Desmodur N3300, Bayer company) is filled into a 1000 ml three-neck flask. The apparatus is equipped with a KPG blade stirrer, a dripping funnel and a gas feed piece to introduce lean air.
El isocianato se diluye con 83,05 g del diluyente reactivo tetracrilato de di-TMP (Ebecryl 140 de Allnex). Además, el modelo se estabiliza con 0,4 g de hidroquinona (de MitsuiChemicals) y posteriormente se calienta la disolución a 40°C.The isocyanate is diluted with 83.05 g of di-TMP tetracrylate reactive diluent (Ebecryl 140 from Allnex). Furthermore, the model is stabilized with 0.4 g of hydroquinone (from MitsuiChemicals) and the solution is subsequently heated to 40 ° C.
Tan pronto se alcanza la temperatura de reacción, se añade gota a gota una mezcla de 133,75 g de mono-acrilato de butanodiol (de BASF SE), 0,05 g de Coscat 83 (de Erbsloh), 49,25 g de diacrilato de hexanodiol (Laromer HDDA de BASF SE), 61 05 g de tetracrilato de di-TMP (Ebecryl 140 de Allnex) y 1,75 g de metoxi-propanol (Solvenon PM de BASF SE). Durante el tiempo de adición (aprox. 4 horas) la temperatura de reacción no puede superar los 60 ° C. Una vez finalizada la adición, se mantiene la mezcla de reacción a 60°C y se determina cada hora el contenido en NCO.As soon as the reaction temperature is reached, a mixture of 133.75 g of butanediol mono-acrylate (from BASF SE), 0.05 g of Coscat 83 (from Erbsloh), 49.25 g of hexanediol diacrylate (Laromer HDDA from BASF SE), 61 05 g of di-TMP tetracrylate (Ebecryl 140 from Allnex) and 1.75 g of methoxy-propanol (Solvenon PM from BASF SE). During the addition time (approx. 4 hours) the reaction temperature cannot exceed 60 ° C. After the addition is complete, the reaction mixture is kept at 60 ° C and the NCO content is determined every hour.
Después de alcanzar el contenido en NCO del 0%, se enfría la mezcla producto a 50 ° C y se filtra.After reaching the NCO content of 0%, the product mixture is cooled to 50 ° C and filtered.
El Coscat 83 es un compuesto de órgano-bismuto que se utiliza como catalizador para la formación de uretano. Empleando ambos acrilatos de uretano antes descritos se elaboraron agentes de recubrimiento curables por radiación. Aquí se utilizaron las siguientes materias primas:Coscat 83 is an organo-bismuth compound that is used as a catalyst for the formation of urethane. Using both of the above described urethane acrylates, radiation curable coating agents were made. The following raw materials were used here:
Según la siguiente Tabla 1 se prepararon agentes de recubrimiento conformes a la invención y no conformes a la invención. Las cifras en la Tabla 1 significan partes en peso. In accordance with the following Table 1, coating agents according to the invention and not according to the invention were prepared. The figures in Table 1 mean parts by weight.
Tabla 1Table 1
Tabla 1 (continuación)Table 1 (continued)
Los agentes de recubrimiento 1 a 12 se aplicaron y curaron de la siguiente manera:Coating Agents 1 through 12 were applied and cured as follows:
La aplicación por pulverización se llevó a cabo con una pistola aerográfica por gravedad (por ejemplo, una pistola de pulverización por gravedad DeVilbiss tipo GTI) con una boquilla de 1,5 mm con una presión de aire comprimido de 3 bar. El grosor de capa requerido se aplicó en dos pasadas de pulverización.The spray application was carried out with a gravity spray gun (for example, a DeVilbiss type GTI gravity spray gun) with a 1.5 mm nozzle with a compressed air pressure of 3 bar. The required layer thickness was applied in two spray passes.
Ventilación: 1 minuto a 23 ° C, 5 minutos a 80 - 90 ° C en un horno de aire forzado, luego 30 segundos de enfriamiento.Ventilation: 1 minute at 23 ° C, 5 minutes at 80 - 90 ° C in a forced air oven, then 30 seconds cool down.
Curado por radiación UV: 2.5 - 3.5 J/cm2 (dosis medida con IL390 de International Light)UV radiation cure: 2.5 - 3.5 J / cm2 (dose measured with IL390 from International Light)
El grosor de capa alcanzado del revestimiento producido a partir del agente de recubrimiento (grosor de película seca) fue de 11-18 mm; el grosor de la llamada " capa IPL" ("capa de interpenetración") fue de 3-5 mm.The achieved layer thickness of the coating produced from the coating agent (dry film thickness) was 11-18 mm; the thickness of the so-called "IPL layer" ("interpenetration layer") was 3-5 mm.
Las mediciones del grosor de la capa se llevaron a cabo con un interferómetro de luz blanca (por ejemplo, de Fuchs con el nombre "FTM-Lite UVNIR - dispositivo de medición del grosor de capa"). El valor de turbidez determinado después de la aplicación de las muestras debe ser <1%.The layer thickness measurements were carried out with a white light interferometer (eg from Fuchs under the name "FTM-Lite UVNIR - layer thickness measuring device"). The turbidity value determined after the application of the samples must be <1%.
La medición de la turbidez se realizó con el aparato de medición "Haze-Gard Plus" de BYK-Gardner. Este aparato de medición es un instrumento estandarizado para medir la transparencia según la norma ASTM D1003-13. El aparato sirve para determinar la calidad óptica de los revestimientos transparentes. Con este aparato de medición se miden la turbidez inicial y la turbidez después de realizar pruebas de rayado (Test de Taber Abraser - o Test Taber de abrasión-).The haze measurement was carried out with the BYK-Gardner "Haze-Gard Plus" measuring device. This measuring device is a standardized instrument for measuring transparency according to ASTM D1003-13. The apparatus is used to determine the optical quality of clear coatings. With this measuring device the initial haze and haze are measured after carrying out scratch tests (Taber Abraser Test - or Taber Abrasion Test-).
La resistencia al rayado de las capas de laca endurecida se probó de la siguiente manera:The scratch resistance of the hardened lacquer layers was tested as follows:
La resistencia al rayado se comprobó utilizando el aparato de ensayo Abraser tipo 5155 de Taber Industries. Las pruebas de rayado se llevaron a cabo y ensayaron según la norma ASTM ASTM-D1044-13 (Método de ensayo estándar para la resistencia de los plásticos transparentes a la abrasión superficial, estándar de ASTM International, 01/09/2013). La evaluación se realizó según la norma ASTM ASTM-D1003-13 (Método de ensayo estándar para la turbidez y la transmisión luminosa de los plásticos transparentes). Scratch resistance was tested using the Abraser Type 5155 Tester from Taber Industries. Scratch tests were carried out and tested according to ASTM ASTM-D1044-13 (Standard Test Method for Resistance of Transparent Plastics to Surface Abrasion, ASTM International Standard, 09/01/2013). The evaluation was performed according to ASTM ASTM-D1003-13 (Standard Test Method for Haze and Light Transmission of Transparent Plastics).
Tabla 2Table 2
EvaluaciónEvaluation
Existe una buena resistencia al rayado de los revestimientos en los soportes de las lámparas de policarbonato cuando muestran un valor de turbidez A15 <15 (después de 300 revoluciones en el test Taber Abraser) al realizar la prueba Taber - Abraser. Los sistemas altamente resistentes a los arañazos muestran un valor de turbidez A inferior a 10 (después de 300 revoluciones en la prueba Taber-Abraser). There is good scratch resistance of coatings on polycarbonate lamp holders when they show a haze value A15 <15 (after 300 revolutions in the Taber Abraser test) when performing the Taber-Abraser test. Highly scratch resistant systems show a haze value A of less than 10 (after 300 revolutions in the Taber-Abraser test).
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| DE4007146A1 (en) * | 1990-03-07 | 1991-09-12 | Basf Ag | RADIATION-curable amine and urea groups containing urethane acrylate compounds |
| DE4200906A1 (en) * | 1992-01-16 | 1993-07-22 | Bayer Ag | USE OF MOISTURIZING VARNISHES BASED ON ORGANIC POLYISOCYANATE FOR THE INTERNAL COATING OF PLASTIC TANKS |
| FR2730239B1 (en) * | 1995-02-02 | 1997-04-25 | Basf Peintures Encres | PLASTIC ICE PROTECTION METHOD FOR VEHICLE HEADLAMPS AND PHOTOPOLYMERIZABLE COMPOSITION USED IN THIS METHOD |
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| US7968197B2 (en) * | 2005-08-25 | 2011-06-28 | Ppg Industries Ohio, Inc. | Polyurea coating comprising an amine/(meth)acrylate oligomeric reaction product |
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| JP2007191530A (en) * | 2006-01-18 | 2007-08-02 | Arakawa Chem Ind Co Ltd | Active energy ray-curable oil in water-type emulsion composition |
| DE102007006492A1 (en) * | 2007-02-09 | 2008-08-14 | Bayer Materialscience Ag | UV-curable dispersions based on polyisocyanates |
| US20090176907A1 (en) * | 2008-01-08 | 2009-07-09 | Ramesh Subramanian | Direct-to-metal radiation curable compositions |
| JP5362430B2 (en) * | 2009-04-27 | 2013-12-11 | 三菱レイヨン株式会社 | Active energy ray-curable composition and molded article |
| KR101782183B1 (en) * | 2009-12-19 | 2017-09-26 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | Low-viscosity polyurethane acrylate dispersions |
| DE102010006755A1 (en) * | 2010-02-04 | 2011-08-04 | BASF Coatings AG, 48165 | Scratch-resistant coated plastic substrates, in particular housings of electronic devices, with high transparency, processes for their production and their use |
| JP5547540B2 (en) * | 2010-04-14 | 2014-07-16 | 関西ペイント株式会社 | Active energy ray-curable coating composition and coated article |
| KR101210905B1 (en) * | 2011-02-25 | 2012-12-11 | 주식회사 케이씨씨 | Uv-curable coating composition useful as top surface coating for plastic substrate and molded article comprisng a cured coating layer formed from the same |
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| JP5664970B2 (en) * | 2011-03-03 | 2015-02-04 | 日油株式会社 | Active energy ray-curable resin composition |
| JP5674729B2 (en) * | 2011-08-31 | 2015-02-25 | 富士フイルム株式会社 | Antistatic hard coat layer forming composition, optical film, method for producing optical film, polarizing plate, and image display device |
| JP5392326B2 (en) * | 2011-09-06 | 2014-01-22 | 株式会社豊田自動織機 | Vehicle member and manufacturing method thereof |
| US9403990B2 (en) * | 2011-09-06 | 2016-08-02 | Kabushiki Kaisha Toyota Jidoshokki | Curing-type coating-agent composition |
| EP2825578B1 (en) * | 2012-03-12 | 2016-05-18 | Byk-Chemie GmbH | Use of polyisocyanate adducts as additives for radiation curable coating compositions |
| JP2014070211A (en) * | 2012-10-01 | 2014-04-21 | Mitsubishi Chemicals Corp | Production method of cyclo olefin-based polymer film with hard coat |
| EP2910612A1 (en) | 2014-02-20 | 2015-08-26 | BASF Coatings GmbH | Coating compositions and coatings prepared from these and their use |
| JP5819506B2 (en) | 2014-11-28 | 2015-11-24 | 三菱樹脂株式会社 | Laminated polyester film |
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